The Gas–liquid Partition Chromatography of Carbohydrate Derivatives: Part I the Separation of Glycitol and Glycose Acetates

Abstract

Gas-liquid partition chro~natography has been used to separate the fully acetylated derivatives of tetritols, pentitols, hexitols, heptitols, octitols, and anomeric glycoses. DISCUSSIONGas-liquid partition chromatography (G.L.P.C.) has already been shown to be a powerful technique for the preparative separation and for the qualitative and quantitative analysis of carbohydrate derivatives. Bishop and his co-workers (1, 2) were the first to report the separation of methyl 0-methyl glycosides by G.L.P.C. and have since demonstrated the use of such separations in the analysis of these derivatives obtained from the fission of methylated polysaccharides (3,4,5). Kircher (6) has also described the G.L.P.C. separation of methylated methyl glycosides employing other types of liquid phases. (7), 0-methyl-0-acetyl glycitols (S), 0-acetyl glycitols (9), and other carbohydrate derivatives (10) have also been successfully resolved using the G.L.P.C. technique. 0-Methyl aldonolactonesIn view of its potential use in the field of carbohydrate chemistry, a systematic program was undertaken in this laboratory t o explore the conditions under which favorable separations of a variety of carbohydrate derivatives inight be undertaken using G.L.P.C. This paper records the results obtained in investigations into the separation of glycitol and glycose acetates. Until recently the methods available for the separation of acetylated glycitols and glycoses involved coluinn chron~atography on a Magnesol-Celite or Silene E F -Celite ( l l a ) mixture using benzene -tert-butyl alcohol as the mobile phase, cellulose column chromatography, or paper chromatography ( l l b ) . I t is considered that the G.L.P.C. method of separation will provide a more rapid and refined procedure.The recorded separations were carried out using samples of the acetate derivatives (2-5 y ) developed on a Pye Gas Argon Chromatograph fitted with an ionization detector (12), and in cases where larger amounts of material (20-200 mg) were used for preparative work, the Burrell Kromo-Tog, Model K-2 apparatus was used. Experience with other types of chromatographic equipment showed that it was necessary for the sample to be injected directly onto the column packing material in order t o prevent the decomposition of the samples, which was observed when a dead space existed between the injection site and the beginning of the column packing material. In this connection it is important t o note that small gaps in the packing material itself should be avoided and that the detector should be placed as close as possible t o the end of column packing for satisfactory results.Acid-washed Chromosorb W or silver-coated Chromosorb W proved to be a suitable inert support which did not show excessive adsorption of the acetate derivatives. The non-polar liquid phases chosen were Apiezoil M vacuum grease or Dow Corning stopcock grease, and the polar phase selected was butailediol succinate polyester. Columns prepared containing 20% w/w of the non-polar liquid phases gave fair separa...

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